Reaction #1702042

Reaction equation

lithium aluminum hydride

ether

sodium potassium tartrate

hydrogen

5-Norbornene-2-carbonitrile

ether

→

5-Norbornene-2-methanamine

Solvents

water

Conditions

Workup

1. 1
   OtherA three-neck flask is equipped with mechanical stirrer
2. 2
   Temperaturereflux condenser
3. 3
   Otherproduces a clear solution
4. 4
   OtherThe reaction solution is transferred to a separatory funnel
5. 5
   Otherthe aqueous phase is collected
6. 6
   Washwashed with 3×50 ml portions of ether
7. 7
   DryingThe combined ether fractions are dried with calcium sulfate and solvent
8. 8
   Otheris removed by rotary evaporation
9. 9
   Otheryielding a yellow oil
10. 10
    workup.DISTILLATIONThis product is further distilled under reduced pressure
11. 11
    Otherto yield a clear oil

Procedure

A three-neck flask is equipped with mechanical stirrer, reflux condenser and dropping funnel. The flask is charged under N2, with 42 ml of a 1.0 M solution of lithium aluminum hydride in anhydrous ether (42 mmol). A solution of 5 g of 5-Norbornene-2-carbonitrile (bicyclo[2.2.1]hept-5-ene-2-carbonitrile) in 45 ml of ether (42 mmol, 1.0 M) is added dropwise through the addition funnel at a rate that allows a gentle reflux. After one hour, the mixture is cooled to 0° C. and water is added dropwise until hydrogen gas liberation is no longer observed. To this, 100 ml of 20% sodium potassium tartrate is added and produces a clear solution. The reaction solution is transferred to a separatory funnel, and the aqueous phase is collected and washed with 3×50 ml portions of ether. The combined ether fractions are dried with calcium sulfate and solvent is removed by rotary evaporation yielding a yellow oil. This product is further distilled under reduced pressure to yield a clear oil.

Source